Methyl 6-amino-5-nitropyridine-3-carboxylate → Methyl 5,6-diaminopyridine-3-carboxylate

HRID 1848064Notes

Reaction equation

HRID 1848064 reaction equation
[NH2:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1>C1COCC1.CO.[Pd]>[NH2:12][C:11]1[C:2]([NH2:1])=[N:3][CH:4]=[C:5]([CH:10]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 1

HCID 13768248Methyl 6-amino-5-nitropyridine-3-carboxylate

Product 1

HCID 9920476Methyl 5,6-diaminopyridine-3-carboxylateYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of methyl 6-amino-5-nitronicotinate (2 g, 10.15 mmol) in a mixture of THF (30 mL) and MeOH (10 mL) at rt was added palladium (10 wt % on activated carbon, 100 mg), and the mixture stirred under hydrogen gas (1 atmosphere) for 15 h. The mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure to afford methyl 5,6-diaminonicotinate (1.69 g, 100%) as a yellow solid which did not require further purification. 1H NMR (300 MHz, DMSO-d6) δ 7.94 (d, J=2.1 Hz, 1H), 7.16 (d, J=2.1 Hz, 1H), 6.27 (br s, 2H), 4.92 (br s, 2H), 3.74 (s, 3H). LCMS (ESI) m/z 168 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-93fc0faadcd846db9ac18f05991ed253
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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